"Very many pleasures are almost only pleasures because we hope and intend to recount them." –Giacomo Leopardi

Capri: Italy’s “StairMaster Isle”

I’m soaking up the warm Italian sunshine on a terrace at Villa Jovis, a Roman villa built for the Emperor Tiberius more than two thousand years ago on the isle of Capri. A lone cloud mars an otherwise faultless blue sky, hovering theatrically like a whiff of smoke above Mount Vesuvius, which towers over the mainland Amalfi Coast.

View of Vesuvius from Villa Jovis

“That was put there by the tourism office,” quips a French tourist, who fell into step alongside my husband Scott and I on our arduous trek to the ruins. Considering all the huffing and puffing we had to do to reach this impressive maze of crumbling walls and archways, I wonder if there’s not a nimbus of steaming perspiration rising from my sizzling flesh, as well.

Piazza Umberto I offers primo people-watching.

Capri’s pulse-raising potential is immediately apparent to passengers aboard the ferry from Naples as it approaches the port of Marina Grande. Wedged atop a rocky bluff, above the marina’s narrow strip of trinket shops and pizzerias, perches the town of Capri—a relatively compact labyrinth of exclusive boutiques and sidewalk cafes populated by beautiful people who have elevated sweater-draping to an art form.

Visitors can surmount the slope on foot, but most opt for the funicular, which deposits travelers just below a gracious terrace where bougainvillea-draped columns frame views of stucco houses tumbling towards the coast. White sails gleam like giant shark fins slicing the surreally teal water, but more menacing still are the formidable cliffs to the west, scarred by a faint zigzag stripe known as the Phoenician Steps.

The view from the terrace atop the funicular.

Until the 1870s, these centuries-old stairs provided the only access between Marina Grande and Capri town’s more relaxed little sister, Anacapri, where shops are more likely to stock authentic local wares than the latest runway fashions. These days, a narrow, winding road skirts the cliff face to connect Anacapri with Capri, providing an adrenaline rush of its own, particularly when riding one of the public buses at night, when the world is enshrouded in inky blackness, save for the marina lights twinkling far, far below. As we round a particularly harrowing bend one evening, even a jaded-looking local is moved to make the sign of the cross, though she coolly attempts to disguise the gesture as a hair toss.

Phoenician Steps, viewed from the top.

Perhaps the Phoenician Steps aren’t such a bad alternative after all, we reason—at least when attempted in broad daylight (and headed down, rather than up).

So we find ourselves at the top of this daunting and seemingly endless staircase, with the colorful fishing boats of Marina Grande bobbing 200 meters below.

Lizards scamper with enviable ease between the big stone steps, rustling among dried leaves and disappearing into weeds, but our thighs and lungs are soon burning.

Towards the bottom, as the steps level out into an alleyway leading into town, we encounter a British couple, already red-faced and panting as they begin the ascent.

The Phoenician Steps, from the base. (Gulp).

“How far to the top?” the wife asks plaintively. “Did you bring a sack lunch?” I reply. Her husband—clearly the instigator of this little adventure–stares daggers at me as I urgently attempt to blink a Morse-code message to the wife: “Forget what Nike says! Just DON’T do it!”

But hubby, undeterred, sweeps her along, and if they made it, they must have experienced a sense of satisfaction at least equal to our own. If we could survive these sadistic steps, then surely we had bested the biggest challenge that “Stairmaster Island” (as my husband Scott nicknames Capri) could boast.

At least, that’s what we think until we undertake the Sentiero dei Fortini, a rocky path linking the ruins of several Napoleonic-era forts along Capri’s wave-lashed west coast.

We begin with lunch at Add O’Riccio, a friendly little restaurant overlooking the Grotta Azzurra, a cave renowned for reflecting the ethereal blue light of the sea. We hoped to take a boat tour of the cave, but the water is too choppy, so after sharing a hearty plate of cheese ravioli and a super-sized Caprese salad (“Grande, like me,” jokes our diminutive waiter), we set off towards the fort course a couple of hundred meters down the road.

Orrico, on the Il Sentiero dei Fortini.

Minutes after descending a short flight of steps to the dirt trail, we’re rewarded with a glimpse of Orrico, the most impressive, in my opinion, of the three forts along the way.

This orderly stone semi-circle seems to have grown out of the jagged precipice upon which it presides, like neatly ordered molecules forming spontaneously from natural chaos.

Though the fort is open to the sky, intriguing features like a brick fireplace remain, and it’s easy to imagine British soldiers gazing pensively out to sea, eyes straining for any sign of the French fleet, who did indeed take Capri in 1808. (The island was returned to the Kingdom of the Two Sicilies in 1813).

Continuing onwards, we pass through a cool forest, where pine needles deaden the sound of our steps. Soon thereafter, we’re evicted into a gray moonscape, clambering over rocks, in and out of gullies, and past blue-fingered fjords and caves that pluck at the eroding limestone.

Painted ceramic plaques beside the path illustrate the flora and fauna that hikers might encounter along the way, such as the rather unimaginatively named “wall lizard,” the Western whip snake (“not poisonous, but prone to bite”), and, somewhat improbably, the Moray eel. If I find myself face to face with an eel, I think, something will have gone drastically, horribly wrong.

Thankfully, we live to hike another day, choosing a trek to the Arco Naturale—a massive natural stone arch on the east coast—as our grand finale. It’s possible to reach the arch via a relatively short walk from Capri town along the Via Matermania. But we’re seduced by the more scenic, albeit longer and more arduous, Via Pizzolungo, which flirts with the southeast coast.

This undulating route proffers fantastic views of the Faraglioni–an array of thrusting pinnacles just offshore—and winds past the Grotta di Matermania, a horseshoe shaped cave that may have played host to ancient fertility rituals. After a final ascent and a jog past the strategically placed Le Grottelle restaurant, we descend one last staircase to view the arch itself.

The Arco Naturale

Rough and unpolished, it shines golden in the sun, offering a keyhole view of the aquamarine sea. As the gray skies that had beleaguered us begin to clear, a rainbow forms just beyond the arch—a celestial confirmation that we’re gazing at one of Capri’s greatest treasures, a priceless view on an island of big bucks and bling.

IF YOU GO

Getting there: Fly into Naples. From Naples, it’s a short taxi or bus ride to Molo Beverello harbour, where you can catch a ferry or jetfoil to Capri. Note: Cars are severely restricted on Capri, but it’s easy to get around using the public buses or taxis.

When to go: Visit between April and October, as many hotels and restaurants close in the winter.

Via Krupp

More walks and hikes: Via Krupp, Capri: Viewed from above, this route, with its hairpin turns carved out of a steep stone slope, resembles a mouse maze as it winds down to the beach at Marina Piccola.

Monte Solaro, Anacapri: You can hoof it to the peak of Monte Solaro, the highest point on the island, in about an hour and a half—or take the chair lift, which hoists you to the top in just over ten minutes. You’ll be rewarded with 360 degree views of the island.

Hotel San Michele. Via G.Orlandi, Anacapri, www.sanmichele-capri.com. This neo-classical property claims the island’s largest swimming pool. Its 65 rooms have balconies or terraces facing either the sea or a mountain slope presided over by the 1,000-year-old Barbarossa Castle.

Hotel Punta Tragara. Via Tragara, Capri, www.hoteltragara.com. About a ten-minute walk from the center of Capri town, this pink stucco beauty boasts two swimming pools, a spa, and 43 rooms and suites, most of which overlook the Faraglioni or Marina Piccolo. Children 12 and under not permitted.

Grand Hotel Quisisana. Via Camerelle, Capri, www.quisisana.com. With its coveted cocktail terrace in the heart of Capri, a pair of swimming pools, tennis courts, and spa treatments, this 150-room, 19th-century grande dame has wooed celebs like Sting and Tom Cruise.